WO2019107196A1 - Composition de caoutchouc de silicone durcissable - Google Patents

Composition de caoutchouc de silicone durcissable Download PDF

Info

Publication number
WO2019107196A1
WO2019107196A1 PCT/JP2018/042583 JP2018042583W WO2019107196A1 WO 2019107196 A1 WO2019107196 A1 WO 2019107196A1 JP 2018042583 W JP2018042583 W JP 2018042583W WO 2019107196 A1 WO2019107196 A1 WO 2019107196A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
same
carbon atoms
silicone rubber
curable silicone
Prior art date
Application number
PCT/JP2018/042583
Other languages
English (en)
Japanese (ja)
Inventor
正和 入江
Original Assignee
ダウ・東レ株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ダウ・東レ株式会社 filed Critical ダウ・東レ株式会社
Priority to US16/767,962 priority Critical patent/US11505703B2/en
Priority to JP2019557156A priority patent/JP7116085B2/ja
Priority to EP18882811.5A priority patent/EP3719075B1/fr
Publication of WO2019107196A1 publication Critical patent/WO2019107196A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5455—Silicon-containing compounds containing nitrogen containing at least one group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

  • the present invention relates to a curable silicone rubber composition having excellent adhesion.
  • a curable silicone rubber composition containing a reaction mixture of an aminoalkylalkoxysilane and an epoxyalkylalkoxysilane see Patent Documents 1 to 3 or cyclic amino acid.
  • a curable silicone rubber composition (see Patent Document 4) containing an alkylsilane has been proposed.
  • An object of the present invention is to provide a curable silicone rubber composition having excellent adhesion to plastics, metals and the like.
  • the composition has the general formula: (Wherein, R 1 is the same or different alkyl group having 1 to 6 carbon atoms, R 2 is the same or different alkyl group having 1 to 3 carbon atoms, R 3 is the same or different alkylene having 2 to 6 carbon atoms And the group a is the same or different integer from 0 to 2.) And 0.1 to 15% by mass of the biuret compound represented by
  • the above biuret compounds have the general formula: NH 2 -R 3 -SiR 1 a (OR 2 ) (3-a) (Wherein, R 1 is an alkyl group having 1 to 6 carbon atoms, R 2 is an alkyl group having 1 to 3 carbon atoms, R 3 is an alkylene group having 2 to 6 carbon atoms, and a is an integer of 0 to 2).
  • the composition is preferably a condensation reaction curable silicone rubber composition, specifically, (A) General formula: (Wherein, R 1 is the same or different alkyl group having 1 to 6 carbon atoms, R 2 is the same or different alkyl group having 1 to 3 carbon atoms, R 3 is the same or different alkylene having 2 to 6 carbon atoms And the group a is the same or different integer from 0 to 2.)
  • the thing which consists of a condensation reaction promotion catalyst of is preferable.
  • the composition is preferably an addition reaction curable silicone rubber composition, specifically, (A) General formula: (Wherein, R 1 is the same or different alkyl group having 1 to 6 carbon atoms, R 2 is the same or different alkyl group having 1 to 3 carbon atoms, R 3 is the same or different alkylene having 2 to 6 carbon atoms And the group a is the same or different integer from 0 to 2.)
  • the catalyst comprises a sufficient amount of a platinum group metal based catalyst to accelerate the reaction.
  • composition is characterized by good adhesion to plastics, metals and the like.
  • composition has the general formula: It is characterized by containing the biuret compound represented by these.
  • R 1 is the same or different alkyl group having 1 to 6 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group and a heptyl group. It is a methyl group.
  • R 2 is the same or different alkyl group having 1 to 3 carbon atoms, and specific examples thereof include a methyl group, an ethyl group and a propyl group, preferably a methyl group and an ethyl group.
  • R 3 is the same or different alkylene group having 2 to 6 carbon atoms, and specific examples thereof include an ethylene group, a propylene group, a butylene group, a pentylene group and a hexylene group, preferably a propylene group.
  • A is the same or different integer from 0 to 2, preferably 0.
  • R 1 , R 2 , R 3 and a are as defined above.
  • aminoalkylalkoxysilanes 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyltriethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane And N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane and N- (2-aminoethyl) -3-aminopropyltriethoxysilane are exemplified, preferably 3-aminopropyltrimethoxysilane .
  • R 1 , R 2 , R 3 and a are as defined above.
  • Examples of such isocyanate alkyl alkoxysilanes include 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropylmethyldimethoxysilane, and 3-isocyanatepropyltriethoxysilane, with preference given to 3-isocyanatepropyltrimethoxysilane.
  • the biuret compound can be prepared by the reaction of the aminoalkylalkoxysilane and the isocyanatealkylalkoxysilane
  • the molar ratio of the aminoalkylalkoxysilane to the isocyanatealkylalkoxysilane is high because the reaction efficiency is high. It is preferably in the range of 1: 1.5 to 1: 3, and particularly preferably in the range of 1: 1.5 to 1: 2.2.
  • organic solvents include aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbons such as toluene and xylene; acetone, methyl isobutyl ketone and the like Ketones; ethers such as diethyl ether and tetrahydrofuran; and esters such as ethyl acetate and isoamyl acetate.
  • the reaction product or reaction mixture thus obtained may be a urea compound in which aminoalkylalkoxysilane and isocyanatealkylalkoxysilane are reacted at a molar ratio of 1: 1, in addition to the biuret compound, or unreacted aminoalkylalkoxysilane or isocyanate.
  • Alkyl alkoxysilanes may remain, but they may be left as long as the object of the present invention is not impaired.
  • the composition contains 0.1 to 15% by mass of the above biuret compound, preferably 0.1 to 10% by mass, 0.1 to 5% by mass, 0.1 to 3% by mass, or 0.1 to 10% by mass. It is characterized by containing 5 to 2% by mass. This is because if the content of the biuret compound is at least the lower limit of the above range, the adhesion of the present composition to plastics, metals, etc. will be improved, while if it is at the upper limit of the above range, the present composition The storage stability of is improved.
  • the curing mechanism of the present composition is not limited.
  • condensation such as dealcohol condensation reaction, dehydration condensation reaction, dehydrogenation condensation reaction, deoxime condensation reaction, deacetic acid condensation reaction, deacetone condensation reaction, dehydroxyamine condensation reaction, etc.
  • Reaction addition reaction; radical reaction by organic peroxide; and others, radical reaction by ultraviolet irradiation.
  • condensation reaction curable present composition (A) the above biuret compound (in the present composition, 0.1 to 15% by mass), (B 1 ) diorganopolysiloxane having molecular chain terminal blocked by silicon-bonded hydroxyl group or silicon-bonded hydrolyzable group, (B 2 ) Silane-based crosslinking agent having a silicon-bonded hydrolysable group in an amount sufficient to crosslink the (B 1 ) component, and (B 3 ) any one for accelerating the condensation reaction of the present composition
  • the thing which consists of a condensation reaction promotion catalyst of this is preferable.
  • the biuret compound of the component (A) is as described above.
  • the silicon-bonded hydrolyzable group in the component (B 1 ) may be a ketoximo group such as a dimethylketoximo group or a methylethyl ketoximo group [sometimes referred to as a ketoximino group, and the general formula: —O—NOCR 4 2 (wherein R 4 represents the same or different alkyl group having 1 to 6 carbon atoms); alkoxy groups such as methoxy and ethoxy; acyloxy groups such as acetoxy; N-butylamino And alkylamino groups such as N, N-diethylamino groups; acylamide groups such as N-methylacetamide groups; N, N-dialkylaminooxy groups such as N, N-diethylaminoxy groups; and alkenyloxy groups such as propenoxy groups
  • an alkoxy group, a ketoximo group, an amino group and an aminoxy group are preferable.
  • alkyl groups such as methyl group, ethyl group, propyl group, butyl group and octyl group; alkenyl groups such as vinyl group, allyl group and hexenyl group; And aryl groups such as tolyl group; and halogenated alkyl groups such as 3,3,3-trifluoropropyl group, 3-chloropropyl group and 3-cyanoalkyl group.
  • the viscosity at 25 ° C. of the component (B 1 ) is not limited, but if the viscosity is too low, the mechanical properties of the cured product become poor, and if the viscosity is too high, the handling workability decreases, so 20-1 It is preferable to be in the range of, 000,000 mPa ⁇ s, or in the range of 100 to 100,000 mPa ⁇ s.
  • the molecular structure of the (B 1 ) component is substantially linear, but part of the molecular chain may be slightly branched.
  • organopolysiloxane units constituting the main skeleton of the component (B 1 ) dimethylpolysiloxane units, methylethylpolysiloxane units, methyloctylpolysiloxane units, methylvinylpolysiloxane units, methylphenylpolysiloxane units, Examples include methyl (3,3,3-trifluoropropyl) polysiloxane units, dimethylsiloxane / methylphenylsiloxane copolymer units, and dimethylsiloxane / methyl (3,3,3-trifluoropropyl) siloxane units.
  • dimethylhydroxysiloxyxylone is a molecular chain terminal blocked by a silicon atom-bonded hydroxyl group.
  • methylphenylhydroxysiloxy group is exemplified, and as a molecular chain end blocked by a silicon atom-bound alkoxy group, vinyldimethoxysiloxy group, methyldimethoxysiloxy group, trimethoxysiloxy group, methyldiethoxysiloxy group, triethoxysiloxy group A group is illustrated.
  • the component (B 2 ) is a silane crosslinking agent having at least two, preferably three or four, silicon-bonded hydrolyzable groups, and has a general formula: R 5 y SiY (4-y) Silane compounds of the general formula: R 6 y Y (3-y) Si-R 7- SiR 6 y Y (3-y) The bis silyl alkane compound represented by these is illustrated.
  • R 5 is a monovalent hydrocarbon group having 1 to 10 carbon atoms, an epoxy group-containing organic group, an amino group-containing organic group, an acrylic group-containing organic group, or a methacryl group-containing organic group.
  • the monovalent hydrocarbon group for R 5 includes alkyl groups such as methyl, ethyl, propyl, butyl and octyl; alkenyls such as vinyl, allyl and hexenyl; and phenyl and tolyl
  • the aryl group include halogenated alkyl groups such as 3,3,3-trifluoropropyl group, 3-chloropropyl group, 3-cyanoalkyl group and the like, with preference given to methyl group.
  • Examples of the epoxy group-containing organic group of R 5 include 3-glycidoxypropyl group, 2- (2,3-epoxycyclohexyl) ethyl group and 3,4-epoxybutyl group.
  • Examples of the amino group-containing organic group of R 5 include 3-aminopropyl group and N- (2-aminoethyl) -3-aminopropyl group.
  • Examples of the acryl group or methacryl group-containing organic group of R 5 include a 3-acryloxypropyl group and a 3-methacryloxypropyl group.
  • Y is a silicon-bonded hydrolyzable group, and the same hydrolyzable group as described above is exemplified, and preferably an alkoxy group, a ketoximo group, an amino group, and an aminoxy group.
  • y is 0 or 1.
  • (B 2 ) component tetramethoxysilane, tetraethoxysilane, n-propyl orthosilicate, methyltrimethoxysilane, methyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, vinyltrimethoxysilane, vinyl tris (2-methoxyethoxy) silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, tetrakis (methylethylketoximo) silane, methyltris (methylethylketoximo) silane, vinyltris (methylethylketoximo) silane, Examples include methyltriacetoxysilane, ethyltriacetoxysilane, methyltriisopropenoxysilane, tetraisopropenoxysilane, and methyltri (N, N-diethyla
  • the content of the (B 2 ) component is an amount sufficient to crosslink the (B 1 ) component, and practically, it is in the range of 2 to 30% by mass of the present composition.
  • the component (B 3 ) is a condensation reaction promoting catalyst for promoting the condensation reaction of the present composition.
  • examples of such (B 3 ) components include organotin compounds such as dibutyltin diacetate, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dimaleate, dioctyltin dilaurate, dioctyltin dimaleate, tin octylate, etc .; Organotitanates such as i-propyl) titanate, tetra (n-butyl) titanate, dibutoxybis (acetylacetonate) titanium, isopropyltriisostearoyl titanate, isopropyl tris (dioctyl pyrophosphate) titanate, bis (dioctyl pyrophosphate) oxyacetate titanate Compounds; tetrabutyl zirconate, tetra
  • an organic tin compound or an organic titanate compound is suitable as the component (B 3 ), and when it is a deoxime condensation reaction, the component (B 3 ) is an organic titanate.
  • Compounds are preferred.
  • the content of the component (B 3 ) is optional, and when it is contained, the content is not particularly limited as long as it is an amount sufficient to promote the condensation reaction of the present composition. Practically, the content is 10% by mass or less, or 5% by mass or less of the present composition, preferably in the range of 0.01 to 10% by mass, or 0.01 to 5% by mass of the composition. It is inside.
  • the addition reaction curable composition of the present invention (A) the above biuret compound (in the present composition, 0.1 to 15% by mass), (C 1 ) organopolysiloxanes having at least two silicon-bonded alkenyl groups in one molecule, (C 2 ) an organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule in an amount sufficient to crosslink the (C 1 ) component, and (C 3 ) the addition of the present composition
  • the catalyst comprises a sufficient amount of a platinum group metal based catalyst to accelerate the reaction.
  • the biuret compound of the component (A) is as described above.
  • the (C 1 ) component is an organopolysiloxane having at least two silicon-bonded alkenyl groups in one molecule.
  • the alkenyl group include a vinyl group, an allyl group, a propenyl group and the like, preferably a vinyl group.
  • the silicon-bonded organic group other than the alkenyl group in the (C 1 ) component is exemplified by methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl and the like.
  • the molecular structure of the (C 1 ) component is not limited, and examples thereof include linear, branched linear, cyclic, and network-like, and preferably linear.
  • the (C 1 ) component may be a single organopolysiloxane or a mixture of two or more organopolysiloxanes. The viscosity at 25 ° C.
  • the component (C 1 ) is not particularly limited, and it can be used from low viscosity liquid to high viscosity gum rubber, but the mechanical properties of the resulting cured product are excellent, so 100 mPas It is preferable that it is s or more.
  • the (C 2 ) component is an organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule.
  • Examples of the silicon-bonded organic group in the component (C 2 ) include alkyl groups such as methyl group, ethyl group and propyl group; aryl groups such as phenyl group and tolyl group; 3,3,3-trifluoropropyl group, 3 Examples thereof include halogen-substituted alkyl groups such as -chloropropyl group.
  • the molecular structure of the (C 2 ) component is not limited, and examples thereof include linear, branched linear, cyclic, dendritic and mesh.
  • the (C 2 ) component may be a single organohydrogenpolysiloxane or a mixture of two or more organohydrogenpolysiloxanes.
  • the viscosity at 25 ° C. of the (C 2 ) component is not limited, it is preferably in the range of 3 to 10,000 mPa ⁇ s.
  • the content of the (C 2 ) component is not particularly limited as long as it is an amount sufficient to crosslink the (C 1 ) component.
  • the ratio of the number of moles of silicon-bonded hydrogen atoms of the (C 2 ) component to the number of moles of silicon-bonded alkenyl groups in the (C 1 ) component is (0.4: 1) to (20: Preferably in an amount of (0.5: 1) to (10: 1), or in an amount of (1: 1) to (3: 1). is there. This is because when the content of the (C 2 ) component is at least the lower limit of the above range, curing of the present composition proceeds sufficiently, while at the same time the upper limit of the above range results in a cured product Because it does not foam.
  • the (C 3 ) component is a platinum group metal catalyst for promoting the addition reaction of the present composition, and examples thereof include chloroplatinic acid, alcohol solutions of chloroplatinic acid, olefin complexes of platinum, vinylsiloxane complexes of platinum, platinum Complexes of acetylene compounds, platinum black, platinum based catalysts such as platinum supported on a solid surface; palladium based catalysts such as tetrakis (triphenylphosphine) palladium; rhodium based catalysts such as chlorotris (triphenylphosphine) rhodium In particular, platinum-based catalysts are preferred.
  • the content of the component (C 3 ) is not particularly limited as long as it is an amount sufficient to promote the addition reaction of the present composition, but practically, the amount of the component (C 3
  • the catalyst metal element in the component) is in an amount of 0.1 to 500 parts by mass, preferably in an amount of 1 to 50 parts by mass. This is because the present composition cures sufficiently if the content of the (C 3 ) component is at least the lower limit of the above range, while coloring at the upper limit of the above range results in coloring of the obtained cured product, etc. Because there are few problems.
  • precipitated silicas are used to adjust the flowability of the present composition or to improve the mechanical strength of the resulting cured product.
  • Reinforcing fillers such as fumed silica, calcined silica, fumed titanium oxide;
  • Non-reinforcing fillers such as crushed quartz, crystalline silica, diatomaceous earth, aluminosilicate, iron oxide, zinc oxide, calcium carbonate, etc. You may mix
  • carbon blacks such as acetylene black, furnace black, channel black, etc .; and further, if necessary, pigments, heat-resistant agents, flame retardants, internal mold release agents, plasticizers, ordinary adhesion promoters, antifungal agents, etc. It is good.
  • the addition reaction curable composition of the present invention may contain a reaction inhibitor to improve its handling workability.
  • reaction inhibitors include alkyne alcohols such as 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, and 2-phenyl-3-butyn-2-ol.
  • Ene compounds such as 3-methyl-3-penten-1-yne and 3,5-dimethyl-3-hexene-1-yne; 1,3,5,7-tetramethyl-1,3,5,7- Examples thereof include tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, and benzotriazole.
  • the content of the reaction inhibitor is not limited, but is in the range of 0.0001 to 5% by mass, preferably in the range of 0.0001 to 2% by mass in the present composition. This is because the pot life of the present composition is improved and the workability is improved when the content of the reaction inhibitor is at least the lower limit of the above range, while the content is at most the upper limit of the above range. This is because the curability of the composition is improved.
  • the viscosity is a value at 25 ° C.
  • Acetylene black (Denka black: made by Denki Kagaku Kogyo Co., Ltd.) 28 parts by mass is added to 72 parts by mass of dimethylsiloxic acid having a viscosity of 9,800 mPa ⁇ s and terminated with trimethylsiloxy group-terminated dimethylpolysiloxane and it becomes uniform at room temperature After mixing up, it was passed through a 3-roll mill for 5 passes to prepare a flowable pigment paste.
  • Example 1 Comparative Examples 1 to 5
  • the condensation reaction curable silicone rubber composition was prepared according to the composition shown in Table 1 using the following components.
  • Silicone rubber base (1) silicone rubber base prepared in Reference Example 3
  • Pigment paste (1) pigment paste prepared in Reference Example 5
  • Pigment paste (2) pigment paste prepared in Reference Example 6
  • Silane crosslinker 1,6-bis (trimethoxysilyl) hexane
  • Adhesion promoter (1) Reaction mixture adhesion promoter prepared in Reference Example 1
  • Reaction mixture adhesion promoter prepared in Reference Example 2 (3): 3-aminopropyltrimethoxysilane adhesion promoter (4) : 3-isocyanatopropyltrimethoxysilane adhesion promoter (5): 3-aminopropyltriethoxysilane
  • a curable silicone rubber composition is applied between two polycarbonate resin adherends (50 mm ⁇ 50 mm ⁇ 5 mm) to a thickness of 1 mm, and then allowed to cure for 30 minutes in an oven at 60 ° C. The The sample was heated at 60 ° C for 30 minutes, and the cured state and adhesiveness were observed and cured. When the adhesiveness was also good, it was evaluated as " ⁇ ", although cured, those with peeling were found to be " ⁇ ", cured. Those that became familiar were evaluated as "x”.
  • Example 2 Comparative Example 6
  • the following components were used to prepare an addition reaction curable silicone rubber composition according to the composition shown in Table 2.
  • Silicone rubber base (2) silicone rubber base prepared in Reference Example 4
  • Crosslinking agent Average unit formula of kinematic viscosity 12 mm 2 / s: [(CH 3 ) 3 SiO 1/2 ] 2 [(CH 3 ) 2 SiO 2/2 ] 7 [(CH 3 ) HSiO 2/2 ] 12 (CH 3 SiO 3/2 ) 1
  • Adhesion promoter (1) reaction mixture prepared in Reference Example 1
  • ⁇ Curable> The following vulcanization characteristics were measured under conditions of 130 ° C./3 minutes by using a curable silicone rubber composition and Curameter III (manufactured by JSR) according to JIS K6300.
  • the curable silicone rubber composition of the present invention has good adhesion to plastics such as polycarbonate resins and metals, etc., and can therefore be suitably used as an adhesive, sealing agent and coating agent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition de caoutchouc de silicone durcissable qui est durcie par une réaction de condensation, une réaction d'addition, etc., et qui contient de 0,1 à 15 % en masse d'un composé biuret représenté par une formule générale (où, R1 est un groupe alkyle identique ou différent ayant de 1à 6 atomes de carbone, R2 est un groupe alkyle identique ou différent ayant de 1 à 3 atomes de carbone, R3 est un groupe alkyle identique ou différent ayant de 2 à 6 atomes de carbone, et a est un nombre entier identique ou différent de 0 à 2). Cette composition de caoutchouc de silicone durcissable présente une adhésion excellente au plastique, au métal, etc.
PCT/JP2018/042583 2017-11-30 2018-11-16 Composition de caoutchouc de silicone durcissable WO2019107196A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US16/767,962 US11505703B2 (en) 2017-11-30 2018-11-16 Curable silicone rubber composition
JP2019557156A JP7116085B2 (ja) 2017-11-30 2018-11-16 硬化性シリコーンゴム組成物
EP18882811.5A EP3719075B1 (fr) 2017-11-30 2018-11-16 Composition de caoutchouc de silicone durcissable

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017-230947 2017-11-30
JP2017230947 2017-11-30

Publications (1)

Publication Number Publication Date
WO2019107196A1 true WO2019107196A1 (fr) 2019-06-06

Family

ID=66664997

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2018/042583 WO2019107196A1 (fr) 2017-11-30 2018-11-16 Composition de caoutchouc de silicone durcissable

Country Status (4)

Country Link
US (1) US11505703B2 (fr)
EP (1) EP3719075B1 (fr)
JP (1) JP7116085B2 (fr)
WO (1) WO2019107196A1 (fr)

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS528854B2 (fr) 1972-01-13 1977-03-11
JPS5541702B2 (fr) 1977-12-08 1980-10-25
JPS6049077A (ja) * 1983-07-01 1985-03-18 ゼネラル・エレクトリツク・カンパニイ 硬化性シリコ−ンの基体への接着を促進するための組成物
JPS60238364A (ja) * 1984-03-14 1985-11-27 ゼネラル・エレクトリツク・カンパニイ 自己接着性室温加硫性シリコ−ン組成物
JPS63500178A (ja) * 1985-04-04 1988-01-21 ロクタイト．コ−ポレ−シヨン 室温加硫性シリコーンゴム組成物
JPS6487660A (en) * 1987-07-13 1989-03-31 Gen Electric N-silylalkylamide and use as adherence improver in room temperature vulcanizable diorganopolysiloxane composition
WO1992007896A1 (fr) * 1990-11-01 1992-05-14 Loctite Corporation FORMULE DE SILICONE DURCISSABLE A L'HUMIDITE ET UTILISANT UN PROMOTEUR D'ADHESION η-UREIDO-PROPYLTRIALCOXYSILANE
JPH0532397B2 (fr) 1987-07-06 1993-05-14 Gen Electric
JPH07113083B2 (ja) 1987-08-28 1995-12-06 東レ・ダウコーニング・シリコーン株式会社 室温硬化性オルガノポリシロキサン組成物
WO2009096050A1 (fr) * 2008-01-28 2009-08-06 Toray Industries, Inc. Compositions de résine siloxane
JP2012025876A (ja) * 2010-07-26 2012-02-09 Shin-Etsu Chemical Co Ltd 室温硬化性オルガノポリシロキサン組成物
JP2012131898A (ja) * 2010-12-21 2012-07-12 Shin-Etsu Chemical Co Ltd 室温硬化性オルガノポリシロキサン組成物及びその製造方法並びに該組成物の硬化物で被覆された物品
WO2014104195A1 (fr) * 2012-12-28 2014-07-03 大阪有機化学工業株式会社 Agent d'amélioration de l'adhérence et composé silane

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4847396A (en) 1985-04-04 1989-07-11 Loctite Corporation Auto-adhering one-component RTV silicone sealant composition utilizing an adhesion promoter
US4826915A (en) 1987-07-13 1989-05-02 General Electric Company N-silylalkylamides and their use as adhesion promoters in room temperature vulcanizable polydiorganosiloxane compositions
JPH0725771B2 (ja) 1992-06-18 1995-03-22 財団法人生産開発科学研究所 ２−アミノエタンスルホン酸亜鉛錯化合物
US5416144A (en) * 1993-12-20 1995-05-16 General Electric Company Addition-curable silicone adhesive compositions and bis (trialkoxysilyalkylene) urea adhesion promoters
JP2004075836A (ja) * 2002-08-19 2004-03-11 Toagosei Co Ltd シーリング材組成物

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS528854B2 (fr) 1972-01-13 1977-03-11
JPS5541702B2 (fr) 1977-12-08 1980-10-25
JPS6049077A (ja) * 1983-07-01 1985-03-18 ゼネラル・エレクトリツク・カンパニイ 硬化性シリコ−ンの基体への接着を促進するための組成物
JPS60238364A (ja) * 1984-03-14 1985-11-27 ゼネラル・エレクトリツク・カンパニイ 自己接着性室温加硫性シリコ−ン組成物
JPS63500178A (ja) * 1985-04-04 1988-01-21 ロクタイト．コ−ポレ−シヨン 室温加硫性シリコーンゴム組成物
JPH0532397B2 (fr) 1987-07-06 1993-05-14 Gen Electric
JPS6487660A (en) * 1987-07-13 1989-03-31 Gen Electric N-silylalkylamide and use as adherence improver in room temperature vulcanizable diorganopolysiloxane composition
JPH07113083B2 (ja) 1987-08-28 1995-12-06 東レ・ダウコーニング・シリコーン株式会社 室温硬化性オルガノポリシロキサン組成物
WO1992007896A1 (fr) * 1990-11-01 1992-05-14 Loctite Corporation FORMULE DE SILICONE DURCISSABLE A L'HUMIDITE ET UTILISANT UN PROMOTEUR D'ADHESION η-UREIDO-PROPYLTRIALCOXYSILANE
WO2009096050A1 (fr) * 2008-01-28 2009-08-06 Toray Industries, Inc. Compositions de résine siloxane
JP2012025876A (ja) * 2010-07-26 2012-02-09 Shin-Etsu Chemical Co Ltd 室温硬化性オルガノポリシロキサン組成物
JP2012131898A (ja) * 2010-12-21 2012-07-12 Shin-Etsu Chemical Co Ltd 室温硬化性オルガノポリシロキサン組成物及びその製造方法並びに該組成物の硬化物で被覆された物品
WO2014104195A1 (fr) * 2012-12-28 2014-07-03 大阪有機化学工業株式会社 Agent d'amélioration de l'adhérence et composé silane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3719075A4

Also Published As

Publication number Publication date
EP3719075A1 (fr) 2020-10-07
EP3719075B1 (fr) 2022-06-15
JP7116085B2 (ja) 2022-08-09
US20200369885A1 (en) 2020-11-26
JPWO2019107196A1 (ja) 2020-11-26
EP3719075A4 (fr) 2021-09-15
US11505703B2 (en) 2022-11-22

Similar Documents

Publication Publication Date Title
JP5997778B2 (ja) 新規アルコキシシリル−エチレン基末端ケイ素含有化合物、室温硬化性オルガノポリシロキサン組成物、及び該組成物を硬化して得られる成形物
JP4775600B2 (ja) 室温硬化性オルガノポリシロキサン組成物
JP6314993B2 (ja) 多成分系室温硬化性オルガノポリシロキサン組成物、該組成物の硬化物及び該硬化物からなる成型物
JP6092491B1 (ja) 室温硬化性ポリオルガノシロキサン組成物およびその調製方法
JP4840602B2 (ja) 室温硬化性オルガノポリシロキサン組成物の硬化方法
JP5960843B2 (ja) アルコキシシリル−エチレン基末端オルガノシロキサンポリマーの製造方法、室温硬化性組成物及びその硬化物である成形物
JP2010215715A (ja) 接着促進剤及び硬化性樹脂組成物
JPWO2008047892A1 (ja) 硬化性ポリオルガノシロキサン組成物
CN101942271A (zh) 从可光交联的聚硅氧烷混合物制造聚硅氧烷涂层和聚硅氧烷成型体的方法
JP2007224089A (ja) 加熱硬化型オルガノポリシロキサン組成物
JP2006265529A (ja) 室温硬化性オルガノポリシロキサン組成物
WO2016117206A1 (fr) Composition d'organopolysiloxane durcissable à température ambiante
JP2004323764A (ja) 接着性ポリオルガノシロキサン組成物
JP2007321123A (ja) 室温硬化性オルガノポリシロキサン組成物
JP2024117823A (ja) 二成分型室温速硬化性オルガノポリシロキサン組成物、該組成物の硬化物及び物品、並びに室温速硬化性オルガノポリシロキサン組成物の硬化方法
JP4864318B2 (ja) 室温硬化性ポリオルガノシロキサン組成物
JP2006131824A (ja) 室温硬化性オルガノポリシロキサン組成物
JP2019059909A (ja) 付加型シリコーン樹脂組成物及びこれを使用した光半導体装置
CN113015775A (zh) 粘接性聚有机硅氧烷组合物
JP2008144042A (ja) 室温硬化性オルガノポリシロキサン組成物
JP7116085B2 (ja) 硬化性シリコーンゴム組成物
JP2010143993A (ja) 室温硬化性ポリオルガノシロキサン組成物
JP2005213487A (ja) 室温硬化性ポリオルガノシロキサン組成物
JP4884601B2 (ja) 室温硬化性ポリオルガノシロキサン組成物
JP6237513B2 (ja) 室温硬化性オルガノポリシロキサン組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18882811

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2019557156

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2018882811

Country of ref document: EP

Effective date: 20200630